The Minnesota Timberwolves certainly didn’t begin their NBA journey as a contender. With their inaugural season coming in 1989-90, the team didn’t win more than 29 games in any of their first seven years. Their first winning season didn’t come until their ninth year in 1997-98, when they went 45-37.
Then, from 2005-06 until 2016-17, the Wolves finished with a losing record every season. Minnesota has had a winning season the last four years though, while making their second and third ever Western Conference finals appearances in the last two. Now, they are getting much closer to exiting the basement as having the worst all-time win percentage amongst the 30 current NBA teams.